Wouldn't a regime with a poor human rights track record consider any use of technology which hides who you are communicating with as warranting further investigation regardless of the ideals behind it? I don't think they are that naive.
But hey, if you decide to use a proxy that screams "I'M A POLITICAL DISSIDENT" with every packet you send they might just get interested.
It's really not as naive as you think.
Hit the nail on the head my good sir.